Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis

Journal of Organic Chemistry

Volumn 81, Issue 16, 2016, Pages 7271-7275

  Patel, Niki R ^a   Molander, Gary A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOLS; SILICATES; SULFUR COMPOUNDS;

ARYL TRIFLATES; DUAL CATALYSIS; ELECTRON-DEFICIENT; ELECTROPHILIC COUPLING; MESYLATES; PHENOL DERIVATIVES; SINGLE ELECTRON; TRANSMETALATION;

CATALYSIS;

NICKEL; PHENOL DERIVATIVE; SILICATE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTROPHILICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PHOTOREDOX NICKEL DUAL CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY;

CARBON-13 MAGNETIC RESONANCE SPECTROSCOPY; CATALYSIS; NICKEL; OXIDATION-REDUCTION; PHENOLS; PHOTOCHEMICAL PROCESSES; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SILICATES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84983301353     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b00800     Document Type: Article

References (39)

1. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
2. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis, 3 rd ed.; University Science: Sausalito, CA, 2010.
3. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433 10.1126/science.1253647
4. Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437 10.1126/science.1255525
5. Osawa, M.; Nagai, H.; Akita, M. Dalton Trans. 2007, 827 10.1039/b618007h
6. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566 10.1021/ja208068w
7. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034 10.1021/ja301553c
8. Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Chem.-Eur. J. 2012, 18, 5170 10.1002/chem.201200050
9. Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505 10.1021/ja400311h
10. Shu, X. Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844 10.1021/ja500716j
11. Tasker, S. Z.; Jamison, T. F. J. Am. Chem. Soc. 2015, 137, 9531 10.1021/jacs.5b05597
12. Corce, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Angew. Chem., Int. Ed. 2015, 54, 11414 10.1002/anie.201504963
13. Jouffroy, M.; Primer, D. N.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 475 10.1021/jacs.5b10963
14. Patel, N. R.; Kelly, C. K.; Jouffroy, M.; Molander, G. A. Org. Lett. 2016, 18, 764 10.1021/acs.orglett.6b00024
15. Jouffroy, M.; Kelly, C. K.; Molander, G. A. Org. Lett. 2016, 18, 876 10.1021/acs.orglett.6b00208
16. Leveque, C.; Chenneberg, L.; Corce, V.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Org. Chem. Front. 2016, 3, 462 10.1039/C6QO00014B
17. Nishigaichi, Y.; Suzuki, A.; Takuwa, A. Tetrahedron Lett. 2007, 48, 211 10.1016/j.tetlet.2006.11.057
18. 2, see: Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
19. Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2015, 137, 2195 10.1021/ja512946e
20. Karakaya, I.; Primer, D. N.; Molander, G. A. Org. Lett. 2015, 17, 3294 10.1021/acs.orglett.5b01463
21. El Khatib, M.; Serafim, R. A. M.; Molander, G. A. Angew. Chem., Int. Ed. 2016, 55, 254 10.1002/anie.201506147
22. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346 10.1021/cr100259t
23. Mesganaw, T.; Garg, N. K. Org. Process Res. Dev. 2013, 17, 29 10.1021/op300236f
24. Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299 10.1038/nature13274
25. Furstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609 10.1002/1521-3773(20020215)41:4<609::AID-ANIE609>3.3.CO;2-D
26. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478 10.1021/ja202769t
27. Agrawal, T.; Cook, S. P. Org. Lett. 2013, 15, 96 10.1021/ol303130j
28. Chen, X.; Quan, Z.-J.; Wang, X.-C. Appl. Organomet. Chem. 2015, 29, 296 10.1002/aoc.3289
29. Doucet, H. Eur. J. Org. Chem. 2008, 2008, 2013 10.1002/ejoc.200700984
30. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810 10.1021/om00004a038
31. Jutand, A.; Mosleh, A. J. Org. Chem. 1997, 62, 261 10.1021/jo961464b
32. Alcazar-Roman, L. M.; Hartwig, J. F. Organometallics 2002, 21, 491 10.1021/om0108088
33. For a detailed computational study of photoredox/nickel dual catalysis utilizing aryl halides, see: Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896 10.1021/ja513079r
34. Li, X.; Wang, W.; Zhang, C. Adv. Synth. Catal. 2009, 351, 2342 10.1002/adsc.200900428
35. Kim, D. W.; Hong, D. J.; Seo, J. W.; Kim, H. S.; Kim, H. K.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2004, 69, 3186 10.1021/jo035563i
36. Guo, X.; Li, C. Org. Lett. 2011, 13, 4977 10.1021/ol202081c
37. Shen, Z.; Goh, K. K. K.; Yang, Y.; Lai, Y.; Wong, C. H. A.; Cheong, H.; Loh, T. Angew. Chem., Int. Ed. 2011, 50, 511 10.1002/anie.201005798
38. Bellale, E. V.; Bhalerao, D. S.; Akamanchi, K. G. J. Org. Chem. 2008, 73, 9473 10.1021/jo801580g
39. Czaplik, W. M.; Mayer, M.; von Wangelin, A. J. Angew. Chem., Int. Ed. 2009, 48, 607 10.1002/anie.200804434